802794
DMPU-HF Reagent
Synonym(s):
DMPU-HF Complex (HF 65% w/w)
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About This Item
Recommended Products
form
liquid
Quality Level
storage temp.
2-8°C
SMILES string
F/O=C1N(C)CCCN\1C
InChI
1S/C6H12FN2O/c1-8-4-3-5-9(2)6(8)10-7/h3-5H2,1-2H3
InChI key
ZTQIVQDBIIEDTI-UHFFFAOYSA-N
Application
DMPU-HF Reagent is a nucleophilic fluorination reagent that can be used:
- To prepare fluoroalkenes and gem-difluoromethlylene from substituted alkynes in the presence of an Au-JohnPhos complex as a catalyst.
- To synthesize substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines from homoallylic alcohol/amine with aldehyde via fluoro-Prins reaction.
- In the bromofluorination of alkenes in the presence of N-bromosuccinimide to yield corresponding bromofluoro compounds.
DMPU-HF, like TREAT-HF and Olah′s Reagent, is a convenient way of utilizing Hydrogen Fluoride as a fluorination reagent. However, unlike TREAT-HF and Olah′s Reagent, DMPU-HF is more tolerant of transition metals due to the reduced basicity of DMPU, compared to Triethylamine and Pyridine. Hammond and coworkers display its compatibility in transition-metal catalysis in gold-catalyzed mono- and difluoroination of alkynes.
Signal Word
Danger
Hazard Statements
Hazard Classifications
Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Skin Corr. 1A
Storage Class Code
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Journal of fluorine chemistry, 203, 136-139 (2018-02-13)
Bromofluorination reactions were performed by treating of a variety of unsaturated compounds with N-bromosuccinimide (NBS) and DMPU/HF as the fluorinating reagent. The DMPU/HF complex showed to be an efficient fluorinating reagent to convert alkenes into their corresponding bromofluoro compounds. It
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